Phospholipid composition of several clinically relevant Corynebacterium species as determined by mass spectrometry: an unusual fatty acyl moiety is present in inositol-containing phospholipids of Corynebacterium urealyticum

Abstract

A comparative study on phospholipids of Corynebacterium amycolatum, Corynebacterium jeikeium and Corynebacterium urealyticum was carried out using fast-atom bombardment (FAB) and electrospray ionization (ESI) mass spectrometry. Data obtained indicate the presence of acylphosphatidylglycerol (APG), diphosphatidylglycerol, phosphatidylglycerol (PG), phosphatidylinositol (PI) and triacylphosphatidylinositol dimannosides (Ac 3 PIM 2 ) in these bacteria. In general, octadecenoyl and hexadecanoyl fatty acyl moieties predominated in phospholipids of C. amycolatum, whereas high levels of hexadecenoyl were found in C. jeikeium and C. urealyticum. Mass spectra from purified APG and PG indicated that the sn-1 position of the glycerol was occupied by octadecenoyl in the three species studied. Notably, several major molecular species of PI and Ac 3 PIM 2 from C. urealyticum contained significant amounts of a moiety identified as 10-methyleneoctadecanoyl, located at the sn-1 position of these molecules. On the other hand, multiantibiotic resistant and susceptible strains of C. amycolatum differed in several minor phospholipid fatty acids of 19 carbon atoms, identified as 10-methyloctadecenoic, 10-methyloctadecanoic (tuberculostearic acid) and 10-methyleneoctadecanoic. The results demonstrate an overall similarity among the phospholipids of the different species studied but also significant differences related to the acyl chains of the glycerol moiety of these compounds, notably the high levels of an unusual fatty acyl moiety in inositol-containing phospholipids of C. urealyticum.

Complete Genome Sequence and Analysis of the Multiresistant Nosocomial PathogenCorynebacterium jeikeiumK411, a Lipid-Requiring Bacterium of the Human Skin Flora

“…The absence of fatty acid synthase apparently results in a strict nutritional requirement of C. jeikeium that has to be supplemented by the availability of exogenous fatty acids in its natural habitats. It was shown recently that C. jeikeium has a cellular fatty acid composition with the majority of these compounds being of the straight-chain, monounsaturated types (83), and it is worth mentioning that the chemical composition of Tween 80 almost exactly meets this requirement of C. jeikeium. Thus, either of the terms "lipid-requiring" or "lipid auxotroph" seems to be more appropriate for the taxonomic description of C. jeikeium isolates than the term "lipophilic."…”

Structural characterization of phosphatidyl-myo-inositol mannosides from Mycobacterium bovis bacillus calmette gúerin by multiple-stage quadrupole ion-trap mass spectrometry with electrospray ionization. II. Monoacyl- and diacyl-PIMs

“…Although ion-trap tandem mass spectrometry with ESI for structural characterization of complex structures of acyl-PIM 2 was recently reported [1], structural detail revealed by multiple-stage ion-trap tandem mass spectrometry has not been described previously.…”

“…The fatty acyl moiety on the inositol can also be identified by the product-ion spectrum from MS 4 of the [M -H -diacylglycerol -R 3 CO 2 H] − ion, which gives rise to a prominent ion corresponding to loss of R 4 CO 2 H. An [M -Hacylmannose] − ion was also observed in the MS 2 -spectra and, thus, the identity of the fatty acid substituent attached to 2-O-mannoside can be confirmed. The combined information obtained from the multiple-stage product-ion spectra from MS 2 , MS 3 , and MS 4 permit the assignment of the complex structures of monoacyl-PIMs and diacyl-PIMs in a mixture isolated from M. bovis Bacillus Calmette Guérin.Although ion-trap tandem mass spectrometry with ESI for structural characterization of complex structures of acyl-PIM 2 was recently reported [1], structural detail revealed by multiple-stage ion-trap tandem mass spectrometry has not been described previously.In the first part of this report, we described the IT multiple-stage mass spectrometric approaches for characterization of PI and PIM molecules from a lipid extract from M. bovis BCG [2]. In this subsequent report, we will describe the structural determination of the monoacyl-and diacyl PIMs in the extract, using the same mass spectrometric approaches.…”

The Family Corynebacteriaceae

“…MK-7(H 2 ) has been detected in Corynebacterium glaucum and Corynebacterium lubricantis, and small amounts of MK-10(H 2 ) have been found in Corynebacterium thomssenii. Phospholipids include phosphatidylglycerol, phosphatidylinositol, phosphatidylinositol dimannosides, and other glycolipids (Yagüe et al 2003). Phosphatidylethanolamine is absent, with the exception of Corynebacterium bovis and Corynebacterium urealyticum.…”